Birthday trip in Tuscany, Italy

How Tuscany Could Become Your Perfect Birthday Trip

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Earlier this year, while I was in Asia, I was already planning for the European summer. Let’s be honest: Asia is incredible during winter, but Europe truly shines in the summer. I could already picture myself sipping wine in Italy, living life like a true Italian. And guess what? Lucky me, that’s exactly what happened!

In June, we booked our flights and embarked on a one-week birthday trip to Tuscany. It turned out to be an absolute blast, and as always, I’m eager to share the experience with you and maybe inspire some ideas for your own adventures. If you’re seeking wine, incredible food, sun-kissed days, and stunning landscapes, then keep reading on!

Best Month to Visit Tuscany

If you’re planning a visit to Tuscany, you might want to skip July and August. According to my personal experience, those months are hot and packed with tourists like gelato lines on a sunny day.

For a cooler and more laid-back experience, go for the shoulder seasons, like May, June, September, or October. That’s when Tuscany is at its magical best! Picture-perfect landscapes, heavenly weather, and fewer crowds – it’s a dream come true!


We went in June, and even though I’m used to tropical heat, some days were already sizzling! And honestly, I’m not sure if it’ll get any better over the years. So, if you’re planning a wine-filled adventure, be mindful of the temperatures, especially in the peak summer months. Choosing cooler seasons might be a smarter move. You don’t want your Tuscan experience or birthday trip to turn into a heatwave showdown!

Tuscany Calling: La Dolce Vita Begins

As you might have gathered by now, I’m not your typical travel guide – because let’s be honest, the internet is brimming with them! Instead, I’m here to share my personal experience, so get ready for a unique perspective on Tuscany. I hope my adventures can inspire you and offer some handy tips!

The birthday trip started in Milan. Why? Because car rentals and flights are much cheaper there. So it was a no-brainer. We went through DiscoverCars, and found the deals interesting. Of course, if you are shorter on time, you might want to rent directly closer, like in Pisa or Florence for example. That’s entirely up to you. Just be sure to check the car you get and then get ready for your road trip adventures. Because if you are going to Tuscany, you need a car. That’s not an option!

Where and How to Start in Tuscany

So, we started off in Milan and drove towards La Spezia because we wanted to spend the first day in Cinque Terre. We stayed in a really nice apartment close to the area – Agriturismo La Villa, I can warmly recommend it. It was conveniently located near La Spezia for the next day’s adventure. For more information about Cinque Terre (by ferry), check out my Cinque Terre blog article. And that was just day 1 of our amazing journey!

Pisa Tower

Day 2 was all about heading to Lucca and Pisa! Yes, Pisa is a total tourist hotspot, but it’s worth the stop. Get those iconic pictures with the Leaning Tower, walk around and indulge in an Italian ice cream.

In the afternoon, we drove straight to my birthday spot. We rented a room in an amazing place with a swimming pool, lush gardens, and views to die for. And oh, the wine! It was pure paradise, and my birthday couldn’t have been celebrated in a more perfect way! You can find the accommodation Podere Benintendi here. We usually book via Booking, it’s easy to use and full of gems.

Tuscany offers endless possibilities, so it all comes down to what floats your boat and how much time you have. What we did is a perfect fit for folks with limited time, who want to soak up the beauty of the Chianti region.

Seriously, there’s a ton of things to explore and experience, and you can totally customize your itinerary based on your interests. Whether you’re into culture, wine tasting, or just getting lost in the Tuscan countryside, you’ll find something that tickles your fancy!

Wine Tasting in Tuscany

Oh my gosh, you won’t believe the awesome surprise we found at our accommodation – a self-service fridge right by the pool filled with incredible wine produced at that agriturismo! It was like hitting the jackpot, and we wasted no time in kicking off the birthday celebrations!

I had one major birthday wish – a wine tasting experience! I mean, we were in Tuscany after all! So, I reached out to a few places, randomly picked one nearby, and did we hit the jackpot again! The tasting was more like a feast with loads of wine flowing. Can you ask for anything better? The place is called Tamburini Winery. You can easily email them for questions or bookings.

Wine tasting in Tuscany

When we visited, they offered two different options:

  • Discover TAMBURINI’S wines (15 euros per person – 45 min) → Wine Tasting of 5 wines + Sweet Wine Vin Santo del Chianti. The wine tasting is combined with Bruschette with their Pure Organic Extra Virgin Olive Oil, and the Vin Santo del Chianti Doc D’Incanto comes with Cantuccini cookies.
  • Full TAMBURINI’S Tour experience (30 euros per person – 2 hours) → This includes a tour of the vinification cellar and storage cellar + Wine Tasting of 7 wines + Vin Santo del Chianti. Combined with Bruschette with their Organic Extra Virgin Olive Oil and traditional Tuscan Salumi. The Vin Santo del Chianti D’incanto is combined with Cantuccini cookies.

We chose the second option, and there was so much more food and specialties than we had planned. It was practically a full lunch! The wine was amazing; our favorite was The Boss Chianti red wine. We loved it so much that we ended up buying some bottles.

Now, I must admit, the afternoon got a tad tough with the heat and all that wine in my system, and we had to skip the restaurant date we had planned. But no worries, we had a brilliant alternative – we decided to grab some pizzas to-go and cozied up in the garden with wine in hand, watching the sunset. The definition of happiness!

Tuscany Charming Towns & Landscapes

When you’re in Tuscany, the real magic lies in hopping in your car and exploring those adorable little towns. It’s all about living the dolce vita! So, my ultimate concept of bliss was simple – have a delightful lunch in one town, and then move on to another for some refreshing drinks. Here are a few to check out:


Renowned for its well-preserved Renaissance walls that encircle the city center, Lucca is a charming and historic city located super close to Pisa, making it easy to combine both visits.

San Gimignano

San Gimignano is a cool spot in Tuscany, known for its medieval vibes and epic towers. But whoa, don’t even think about grabbing drinks on the main piazza (Piazza della Cisterna)! They charged something like 7 euros for a can of coke. Go for wine instead; it’s way cheaper! Actually, the real deal here is indulging in the BEST ice cream you’ll ever taste at Gelateria Dondoli!


This city is a must-see, no doubt about it. Art, architecture, history – it’s a grand slam of awesomeness!


Siena, it’s like stepping back in time with its medieval streets and captivating architecture. The heart of Siena is its stunning Piazza del Campo, where you can feel the vibrant energy of the city. And guess what? It’s not too far from Florence, so you can easily add it to your Tuscan adventure.


We visited this town on another Tuscany adventure, but I had to talk about it here. I truly fell in love with the town. You can’t, and I repeat, can’t skip this one! It’s got that Tuscan magic that will steal your heart!

Tips for Future Tuscany Travellers

  • Let’s talk about parking – if you’re exploring Tuscany with a car (which I hope you are!), you might stress about finding spots. But everywhere we went, we discovered free parking! Just do a quick internet search, and you’ll find sweet spots. Sometimes it involves a bit of walking, but that’s just a perfect excuse to indulge in more pizza guilt-free!
  • Now, hydratation is the key when it’s hot. Tuscany’s got your back with water fountains scattered around. Refill your water bottle whenever you spot one. Not only does it save you some bucks, but it’s also eco-friendly – double win!

Wrapping Up: Tuscany, The Perfect Birthday Trip

I guess you got it. My Tuscany birthday trip was absolutely incredible, and I can’t help but gush about it. It’s a definite must-do (and not only on your birthday)! I had the time of my life, and I’m totally on board with recommending it to anyone and everyone.

Oh, and if you’ve got some extra time, I’d highly suggest adding a side trip to Cinque Terre. Of course, there is so much more to see in Tuscany but what we did already gives you a great Tuscan taste.

And if you are yearning for more Italian escapades, check out my blog article about Genoa. It’s a fantastic Italian weekend getaway.

Thank you for joining me on this Tuscany adventure, and I hope it inspires you to embark on your own escapades.

Until the next wanderlust-filled tale, arrivederci!

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